Synthesis of 2-(2-hydroxyaryl)alkenylphosphonium salts from phosphine oxides via ring-closing ring-opening approach and their antimicrobial evaluation

Татаринов, Д. А.; Kuznetsov, Denis M.; Voloshina, Alexandra D.; Lyubina, Anna P.; Strobykina, A. S.; Мухитова, Ф. К.; Polyancev, Fedor M.; Миронов, В. Ф.

doi:10.1016/j.tet.2016.11.023

Cited by 22 publications

(20 citation statements)

References 35 publications

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“…PP1 (( Z )-(2-(5-chloro-2-hydroxyphenyl)2-phenylvinyl)(methyl)diphenylphosphonium chloride), PP2 (( Z )-(2-(5-chloro2-hydroxyphenyl)2-phenylvinyl)(ethyl)diphenylphosphonium chloride), PP3 (( Z )-(2-(5-chloro2-hydroxyphenyl)2-phenylvinyl)(propyl)diphenylphosphonium chloride), PP4 (( Z )-(2-(5-chloro2-hydroxyphenyl)2-phenylvinyl)(butyl)diphenylphosphonium chloride), PP5 (( Z )-(2-(5-chloro2-hydroxyphenyl)2-phenylvinyl)(pentyl)diphenylphosphonium chloride), and PP6 (( Z )-(2-(5-chloro2-hydroxyphenyl)2-phenylvinyl)(hexyl)diphenylphosphonium chloride) were synthesized as described earlier …”

Section: Experimental Sectionmentioning

confidence: 99%

“…In view of these results, appending phenol derivatives to phosphonium cations can be proposed as an approach for creating zwitterionic protonophores. Previously, we reported synthesis of 2-(2-hydroxyaryl)alkenylphosphonium salts–derivatives of a substituted phenol linked with quaternary phosphonium having one alkyl (R) and two phenyl (P) substituents (PPR) by a newly developed method . The advantages of the new approach to synthesis of QPCs from phosphine oxides were recently highlighted in …”

Section: Introductionmentioning

confidence: 99%

“…The PPR with a hexyl substituent (PP6) exhibited strong antibacterial activity . According to a series of recent papers, − the antibacterial activity of certain classes of compounds is associated with collapsing the proton motive force on the bacterial membrane via the protonophoric mechanism.…”

Section: Introductionmentioning

confidence: 99%

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Zwitterionic Protonophore Derived from 2-(2-Hydroxyaryl)alkenylphosphonium as an Uncoupler of Oxidative Phosphorylation

et al. 2019

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2-(2-Hydroxyaryl)alkenylphosphonium salts (here coined as PPR) representing derivatives of quaternary phosphonium with two phenyl (P) and one alkyl (R) substituents linked through alkenyl bridge to substituted phenol were applied here to planar bilayer lipid membranes (BLM), isolated mitochondria, and cell culture. PPR with six carbon atoms in R (PP6) induced proton-selective currents across BLM and caused mitochondrial uncoupling. In particular, PP6 at submicromolar concentrations accelerated respiration, decreased membrane potential, and reduced ATP synthesis in isolated rat liver mitochondria (RLM). Methylation of a hydroxyl group substantially suppressed the protonophoric activity of PP6 on BLM and its uncoupling potency in RLM. Of note, the methylated derivative PP6-OMe was synthesized here via a new synthetic route including cyclization of PP6 with subsequent ring opening. PPR were considered as protonophoric uncouplers of a zwitterionic type, capable of penetrating membranes both as a zwitterion composed of a deprotonated phenol and a cationic quaternary phosphonium, and as a protonated cation. The protonophoric and uncoupling properties of PPR found here were speculated to account for their strong antibacterial activity described previously.

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Section: Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Zwitterionic Protonophore Derived from 2-(2-Hydroxyaryl)alkenylphosphonium as an Uncoupler of Oxidative Phosphorylation

et al. 2019

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“…Bactericidal and fungicidal activities, which cause the death of the microbial cells, were determined using literature procedures. 47,48 The tests were performed in duplicate and repeated twice.…”

Section: Biological Evaluationmentioning

confidence: 99%

Design, synthesis, and biological activity of novel ammonium salts containing sterically hindered phenolic fragment and phosphoryl group

et al. 2018

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“…19,20 Finally, quaternary phosphorus salt and silver-bearing compounds are traditional antibacterial materials, their hybridization will help improve antibacterial performance. 21,22 In this work, alkyl-bis-(triphenyl)phosphoniums with different spacer lengths (spacer n=2, 3, 4) were used as organic templates to obtain three new bromoargentate hybrids, ie, (…”

Section: Introductionmentioning

confidence: 99%

<p>Multifunctional Quaternary Phosphorus/Bromoargentate Hybrids: The Achievement of Greenish Blue Luminescence, Repeatable Photocurrent Responses and Durable Antimicrobial Activities with Enhanced Water Stability</p>

Liu

Zhang

et al. 2020

IJN

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Background: The realization of multifunction in one bulk material is fascinating for developing a new generation of devices. Quaternary phosphorus salts were seldom utilized as templates in haloargentate systems, and the hybridization of alkyl(triphenyl)phosphonium with halometallate will be a good strategy for the development of multifunctional material, especially for biological material. Methods: Under the template of (triphenyl)phosphonium-based quaternary phosphorus salts with different spacer lengths (n=2, 3, 4), three bromoargentate hybrids were constructed via the solution method, ie, (1,2-DBTPP)(Ag 2 Br 4) (1), {(1,3-DBTPP) 2 (Ag 7 Br 11)]•CH 3 CN•H 2 O} n (2), and {[(1,4-DBTPP)(Ag 5 Br 7)](CH 3 CN) 2 •H 2 O} n (3) (1,2-DBTPP 2+ =ethane-1,2-diylbis (triphenyl)phosphonium, 1,3-DBTPP 2+ =propane-1,3-diylbis (triphenyl)phosphonium, 1,4-DBTPP 2 + =butane-1,4-diylbis (triphenyl)phosphonium)). Results: The (Ag 7 Br 11) n 4nchain in 2 is a new type of 1-D bromoargentate chain constructed from cubane-like Ag 4 Br 4 nodes, AgBr 4 tetrahedrons and AgBr 3 triangles. Interestingly, by elongating spacer n from 2 to 4, argentophilicity interactions are weakened, and the hydrogen bonds are strengthened. Consequently, their water stabilities and photocurrents are improved, in which the Ag-4d/Br-4p to π* anti-bonding orbital of the quaternary phosphorus transfer is facilitated. Furthermore, the greenish blue emissions can be detected. Finally, high inhabitation rates against Streptococcus mutans and Candida albicans can be observed in 2 and 3. Conclusion: In all experiments, by elongating the spacer lengths of quaternary phosphorus salts, multifunctions were integrated in the quaternary phosphorus/bromoargentate hybrids, including greenish blue luminescence, repeatable photocurrent responses and durable antimicrobial activities with enhanced water stability. This work could provide a theoretical guide for the design of new biologically multifunctional materials.

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Synthesis of 2-(2-hydroxyaryl)alkenylphosphonium salts from phosphine oxides via ring-closing ring-opening approach and their antimicrobial evaluation

Cited by 22 publications

References 35 publications

Zwitterionic Protonophore Derived from 2-(2-Hydroxyaryl)alkenylphosphonium as an Uncoupler of Oxidative Phosphorylation

Zwitterionic Protonophore Derived from 2-(2-Hydroxyaryl)alkenylphosphonium as an Uncoupler of Oxidative Phosphorylation

Design, synthesis, and biological activity of novel ammonium salts containing sterically hindered phenolic fragment and phosphoryl group

<p>Multifunctional Quaternary Phosphorus/Bromoargentate Hybrids: The Achievement of Greenish Blue Luminescence, Repeatable Photocurrent Responses and Durable Antimicrobial Activities with Enhanced Water Stability</p>

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